Phenanthrene, phase

Weak to moderate chemiluminescence has been reported from a large number of other Hquid-phase oxidation reactions (1,128,136). The Hst includes reactions of carbenes with oxygen (137), phenanthrene quinone with oxygen in alkaline ethanol (138), coumarin derivatives with hydrogen peroxide in acetic acid (139), nitriles with alkaline hydrogen peroxide (140), and reactions that produce electron-accepting radicals such as HO in the presence of carbonate ions (141). In the latter, exemplified by the reaction of h on(II) with H2O2 and KHCO, the carbonate radical anion is probably a key intermediate and may account for many observations of weak chemiluminescence in oxidation reactions. 

An important development has been the isolation of bacteria that were able to degrade phenan-threne that was sorbed to humic acid material (Vacca et al 2005). Enrichment was carried ont with PAH-contaminated soils using phenanthrene sorbed to commercial hnmic acid. Only the strains isolated from this enrichment were able to carry ont degradation of C-labeled phenanthrene, and this exceeded by factors of 4-9 the amonnt estimated to be available from the aqneons phase alone. It was snggested that specially adapted bacteria might interact specifically with natnrally occnrring colloidal material. 

Sander and wise have proposed a test method to determine the bonding chemistry used to prepare octadecylsiloxane column packings based on the relative retention of three polycyclic aromatic hydrocarbons, benzo[a]pyrene (BaP), phenanthro-phenanthrene (PhPh), and l,2 3,4 5,6 7,8-tetrabenzonaphthalene (TBN) eluted with the mobile phase acetonitrile-water (85 15) [52,67,199,210]. On monomeric phases the test solutes elute in the... 

Fig. 5. Relationship between the log Koc for phenanthrene sorption and the aliphaticity of humic acids, sequentially extracted from a soil. F-l, F-4, F-7, and F-9 are the first, fourth, seventh, and nineth extracted humic acids, respectively. 0.005, 0.05, and 0.5 pg mL are selected liquid-phase equilbrium concentrations of phenanthrene (Kang and Xing 2005).

Feng Y, Park JH, Voice TC, Boyd SA (2000) Bioavailability of soil-sorbed biphenyl to bacteria. Environ Sci Technol 34 1977-1984 Friedrich M, Grosser RJ, Kern EA, Inskeep WP, Ward DM (2000) Effect of model sorptive phases on phenanthrene biodegradation molecular analysis of enrichments and isolates suggests selection based on bioavailability. Appl Environ Microbiol 66 2703-2710... 

Biermann, H.W., MacLeod, H., Atkinson, R., Winer, A.M., Pitts Jr., J.N. (1985) Kinetics of the gas-phase reactions of the hydroxyl radical with naphthalene, phenanthrene and anthracene. Environ. Sci. Technol. 19, 244—248. 

Carroquino, M.J. and M. Alexander. 1998. Factors affecting the biodegradation of phenanthrene initially dissolved in different nonaqueous-phase liquids. Environ. Toxicol. Chem. 17 265-270. 

Micelles forming above the c.m.c. incorporate hydrophobic molecules in addition to those dissolved in the aqueous phase, which results in apparently increased aqueous concentrations. It has to be noted, however, that a micelle-solubilised chemical is not truly water-dissolved, and, as a consequence, is differently bioavailable than a water-dissolved chemical. The bioavailability of hydrophobic organic compounds was, for instance, reduced by the addition of surfactant micelles when no excess separate phase compound was present and water-dissolved molecules became solubilised by the micelles [69], In these experiments, bacterial uptake rates were a function of the truly water-dissolved substrate concentration. It seems therefore that micellar solubilisation increases bioavailability only when it transfers additional separate phase substrate into the aqueous phase, e.g. by increasing the rates of desorption or dissolution, and when micelle-solubilised substrate is efficiently transferred to the microorganisms. Theoretically, this transfer can occur exclusively via the water phase, involving release of substrate molecules from micelles, molecular diffusion through the aqueous phase and microbial uptake of water-dissolved molecules. This was obviously the case, when bacterial uptake rates of naphthalene and phenanthrene responded directly to micelle-mediated lowered truly water-dissolved concentrations of these chemicals [69]. These authors concluded from their experiments that micellar naphthalene and phenanthrene had to leave the micellar phase and diffuse through the water phase to become... 

Guha, S. and Jaffe, P. R. (1996). Biodegradation kinetics of phenanthrene partitioned into the micellar phase of nonionic surfactants, Environ. Sci. Technol., 30, 605 611. 

Aromatic molecules with no polar substituent include benzene derivatives or other, more polyaromatic molecules, such as naphthalene, phenanthrene, and anthracene. These are polarizable. Paraffins are not polarizable by comparison. In gas-liquid systems, aromatic molecules will show stronger interactions with polar stationary phases that paraffins of comparable boiling point and, thus, polar stationary phases can aid in improving separation of substituted aromatics. 

Fig. 16. CEC separation of naphthalene (1), fluorene (2), phenanthrene (3), anthracene (4), pyrene (5),triphenylene (6),andbenzo(a)pyrene (7) using capillary filled with CIO alkyl substituted polyallylamine. (Reprinted with permission from [86]. Copyright 1997 Elsevier). Conditions capillary 50 pm i.d., 48 cm total length, 33 cm active length, field strength 400 V/cm, carrier concentration 20 mg/ml, mobile phase 60 40 methanol-20 mmol/1 borate buffer pH=9.3...

The arene (5 mmol) in CHCl3 (100 ml) is added to aqueous NaOCl (0.6 M, 250 ml) and the pH is adjusted to 8-9 by the addition of cone. HCl. TBA-HS04 (0.34 g, l mmol) is added and the mixture is stirred until TLC analysis shows complete conversion of the arene. The organic phase is separated, washed well with H20, dried (K2CO ), and evaporated to yield the epoxide (e.g. 90% from phenanthrene, 76% from 1,2-benz-anthracene, 70% from acenaphthene, 19% 2,3 4,5-bis-epoxide from naphthalene). 

Phase transition models, oscillatory reactions, 39 92-97 Phenanthrene... 

Some PAHs (e.g., phenanthrene, pyrene, and benzo[g,/z,i]perylene) are commonly seen in products boiling in the middle to heavy distillate range. In a method for their detection and analysis (EPA 8310), an octadecyl column and an aqueous acetonitrile mobile phase are used. Analytes are excited at 280 nm and detected at emission wavelengths of >389 nm. Naphthalene, acenaphthene, and fluorene must be detected by a less sensitive UV detector because they emit light at wavelengths below 389 nm. Acenaphthylene is also detected by UV detector. 

SRM 869a Column Selectivity Test Mixture for Liquid Chromatography [44] is composed of three shape-constrained PAHs (phenanthro[3,4-c]phenanthrene, PhPh l,2 3,4 5,6 7,8-tetrabenzonaphthalene, TBN and benzo[a]pyrene, BaP) and is routinely employed to evaluate the shape selectivity of stationary phases. The retention differences between the nonplanar TBN and planar BaP solutes (expressed as a selectivity factor axEN/BaP = provide a numerical assessment of... 

Fujimoto et al. [77] synthesized a novel phase by coupling a dodecylamino-substituted P-cyclodextrin (P-CD) to 3-glycidoxypropyl-derivatized silica gel. The surface coverage of this phase was reported as 0.37 xmol/m, which amounts to a surface coverage of 2.6 xmol/m for C12 chains (seven chains per fi-CD). An increase in shape selectivity was observed when compared with a conventional Cis monomeric phase as determined by selectivity differences between j9/m-terphenyl, j9/o-terphenyl, and coronene/phenanthro[3,4-c]phenanthrene solute pairs and was attributed to the localized high ligand density as constrained by the fi-CD platform structure. 

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